Trifluoroacetic acid → HCID 178522004, compound

HRID 1521770Notes

Reaction equation

HRID 1521770 reaction equation
[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9]3[N:15]=[C:14]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5[N:26]=[CH:27][N:28](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:29]=5)[CH:20]=4)=[O:17])[CH:13]=[CH:12][C:10]=3[CH:11]=[C:3]12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[CH:29]=[C:25]([C:21]2[CH:20]=[C:19]([NH:18][C:16]([C:14]3[CH:13]=[CH:12][C:10]4[CH:11]=[C:3]5[C:2](=[O:1])[NH:8][CH2:7][CH2:6][CH2:5][N:4]5[C:9]=4[N:15]=3)=[O:17])[CH:24]=[CH:23][CH:22]=2)[N:26]=[CH:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672372246-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide

Product 1

HCID 178522004HCID 178522004, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide (86 mg, 0.14 mmol) in CH2Cl2 (1 mL) is added TFA (0.5 mL). The mixture is stirred at room temperature for 16 hr then is concentrated under reduced pressure. The residue is purified via preparative HPLC using a gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA to afford the title compound (25 mg, 47%). LCMS: 387.86 (M+H+). (System T-med polar) Table 3 below, lists the mass spectral data and the HPLC retention times for Examples 1 to 105.

Workup

  1. concentrationthen is concentrated under reduced pressure
  2. customThe residue is purified via preparative HPLC
  3. washa gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA

Sources & evidence

ORD record
ord-38eec52f48b748628f162095f25007be
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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